##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
                                             
data_global
_audit_creation_method     'form.cif (version 2.0)'
_journal_data_validation_number     ?
_journal_date_recd_electronic     2010-08-14
_journal_date_accepted     2010-08-17
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2010
_journal_volume     66
_journal_issue      9
_journal_page_first     o2370
_journal_page_last     o2371
_journal_paper_category     QO
_journal_coeditor_code     CI5154
_publ_contact_author_name     'Prof. Fun, Hoong-Kun'
_publ_contact_author_address
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      MALAYSIA
;
_publ_contact_author_email     'hkfun@usm.my'
_publ_contact_author_fax     '6 04 6579150'
_publ_contact_author_phone     '6 04 6533652'
_publ_section_title
;\
2-Hydroxy-11-methyl-16-[(E)-4-methylbenzylidene]-13-(4-methylphenyl)-1,\
11-diazapentacyclo[12.3.1.0^2,10^.0^3,8^.0^10,14^]octadeca-3(8),4,6-triene-\
9,15-dione
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Raju Suresh Kumar' ?
;
      School of Chemical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hasnah Osman' ?
;
      School of Chemical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Mohamed Ashraf Ali' ?
;
      School of Physical Sciences
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Chin Sing Yeap'
;
Thomson Reuters ResearcherID: A-5523-2009.
;
;
      X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
    'Hoong-Kun Fun'
;
Thomson Reuters ResearcherID: A-3561-2009.
;
;     X-ray Crystallography Unit
      School of Physics
      Universiti Sains Malaysia
      11800 USM, Penang
      Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Hydroxy-11-methyl-16-[(E)-4-methylbenzylidene]-13-(4-methylphenyl)-
1,11-diazapentacyclo[12.3.1.0^2,10^.0^3,8^.0^10,14^]octadeca-3(8),4,6-triene-
9,15-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C32 H30 N2 O3'
_chemical_formula_sum     'C32 H30 N2 O3'
_chemical_formula_iupac     'C32 H30 N2 O3'
_chemical_formula_weight     490.58
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     9.3252(6)
_cell_length_b     12.1781(8)
_cell_length_c     12.9821(8)
_cell_angle_alpha     67.480(2)
_cell_angle_beta     86.093(2)
_cell_angle_gamma     69.475(2)
_cell_volume     1271.68(14)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     9995
_cell_measurement_theta_min     5.75
_cell_measurement_theta_max     67.75
_cell_measurement_temperature     100
_exptl_crystal_description     Plate
_exptl_crystal_colour     yellow
_exptl_crystal_size_max     0.56
_exptl_crystal_size_mid     0.29
_exptl_crystal_size_min     0.25
_exptl_crystal_density_diffrn     1.281
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     520
_exptl_absorpt_coefficient_mu     0.653
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2009)'
_exptl_absorpt_correction_T_min     0.7127
_exptl_absorpt_correction_T_max     0.8511
_exptl_special_details
;
The crystal was placed in the cold stream of an Oxford Cryosystems Cobra
open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
;
_diffrn_ambient_temperature     100
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker APEXII DUO CCD area-detector'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     13699
_diffrn_reflns_av_R_equivalents     0.0240
_diffrn_reflns_av_sigmaI/netI     0.0226
_diffrn_reflns_theta_min     6.05
_diffrn_reflns_theta_max     64.99
_diffrn_reflns_theta_full     64.99
_diffrn_measured_fraction_theta_max     0.952
_diffrn_measured_fraction_theta_full     0.952
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -14
_diffrn_reflns_limit_k_max     14
_diffrn_reflns_limit_l_min     -15
_diffrn_reflns_limit_l_max     15
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     4121
_reflns_number_gt     4004
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0478
_refine_ls_R_factor_gt     0.0444
_refine_ls_wR_factor_gt     0.1232
_refine_ls_wR_factor_ref     0.1338
_refine_ls_goodness_of_fit_ref     1.205
_refine_ls_restrained_S_all     1.205
_refine_ls_number_reflns     4121
_refine_ls_number_parameters     342
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0743P)²+0.3694P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.317
_refine_diff_density_min     -0.396
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.069(4)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'N' 'N' 0.0311 0.0180
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'APEX2 (Bruker, 2009)'
_computing_cell_refinement     'SAINT (Bruker, 2009)'
_computing_data_reduction     'SAINT (Bruker, 2009)'
_computing_structure_solution     'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXTL (Sheldrick, 2008)'
_computing_molecular_graphics     'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.69853(13) 0.26369(11) 0.55957(9) 0.0290(3) Uani d . 1 . .
    O O2 1.14244(12) -0.01927(10) 0.92987(8) 0.0219(3) Uani d . 1 . .
    O O3 0.90572(13) -0.06206(11) 0.65669(9) 0.0296(3) Uani d . 1 . .
    N N1 1.02023(14) 0.19002(11) 0.79859(10) 0.0195(3) Uani d . 1 . .
    N N2 0.87997(14) -0.05467(11) 0.88897(10) 0.0213(3) Uani d . 1 . .
    C C1 1.18437(18) 0.39376(14) 0.46558(13) 0.0255(4) Uani d . 1 . .
    H H1A 1.1585 0.4127 0.5288 0.031 Uiso calc R 1 . .
    C C2 1.30607(19) 0.42114(15) 0.40771(14) 0.0306(4) Uani d . 1 . .
    H H2A 1.3609 0.4577 0.4332 0.037 Uiso calc R 1 . .
    C C3 1.3481(2) 0.39515(16) 0.31222(15) 0.0344(4) Uani d . 1 . .
    C C4 1.2616(2) 0.34286(17) 0.27535(15) 0.0374(4) Uani d . 1 . .
    H H4A 1.2859 0.3264 0.2108 0.045 Uiso calc R 1 . .
    C C5 1.1405(2) 0.31491(16) 0.33248(14) 0.0314(4) Uani d . 1 . .
    H H5A 1.0848 0.2800 0.3056 0.038 Uiso calc R 1 . .
    C C6 1.09964(18) 0.33786(14) 0.42997(12) 0.0238(4) Uani d . 1 . .
    C C7 0.97216(17) 0.30238(13) 0.48655(12) 0.0230(4) Uani d . 1 . .
    H H7A 0.9031 0.2979 0.4412 0.028 Uiso calc R 1 . .
    C C8 0.93923(17) 0.27523(13) 0.59393(12) 0.0207(3) Uani d . 1 . .
    C C9 0.80311(17) 0.23458(13) 0.62724(12) 0.0215(3) Uani d . 1 . .
    C C10 0.80285(17) 0.15433(13) 0.75147(12) 0.0202(3) Uani d . 1 . .
    C C11 0.85546(16) 0.21946(13) 0.81648(12) 0.0202(3) Uani d . 1 . .
    H H11A 0.8003 0.3104 0.7865 0.024 Uiso calc R 1 . .
    H H11B 0.8398 0.1847 0.8954 0.024 Uiso calc R 1 . .
    C C12 1.03611(17) 0.27348(14) 0.68483(12) 0.0208(3) Uani d . 1 . .
    H H12A 1.1432 0.2463 0.6690 0.025 Uiso calc R 1 . .
    H H12B 1.0074 0.3593 0.6820 0.025 Uiso calc R 1 . .
    C C13 0.52758(18) 0.21075(15) 0.92567(13) 0.0279(4) Uani d . 1 . .
    H H13A 0.6058 0.1488 0.9792 0.033 Uiso calc R 1 . .
    C C14 0.4105(2) 0.29883(16) 0.95461(14) 0.0324(4) Uani d . 1 . .
    H H14A 0.4123 0.2955 1.0273 0.039 Uiso calc R 1 . .
    C C15 0.29066(19) 0.39205(16) 0.87786(15) 0.0333(4) Uani d . 1 . .
    C C16 0.29137(19) 0.39398(16) 0.77021(15) 0.0333(4) Uani d . 1 . .
    H H16A 0.2117 0.4547 0.7174 0.040 Uiso calc R 1 . .
    C C17 0.40876(18) 0.30691(15) 0.74029(14) 0.0282(4) Uani d . 1 . .
    H H17A 0.4070 0.3106 0.6675 0.034 Uiso calc R 1 . .
    C C18 0.52947(17) 0.21387(14) 0.81723(13) 0.0233(4) Uani d . 1 . .
    C C19 0.65657(17) 0.12088(14) 0.78116(12) 0.0227(4) Uani d . 1 . .
    H H19A 0.6158 0.1213 0.7133 0.027 Uiso calc R 1 . .
    C C20 0.71422(18) -0.01858(14) 0.86592(13) 0.0250(4) Uani d . 1 . .
    H H20A 0.6621 -0.0261 0.9342 0.030 Uiso calc R 1 . .
    H H20B 0.6947 -0.0732 0.8347 0.030 Uiso calc R 1 . .
    C C21 0.93759(16) 0.02464(13) 0.79105(12) 0.0199(3) Uani d . 1 . .
    C C22 0.98737(18) -0.02951(13) 0.69987(12) 0.0223(3) Uani d . 1 . .
    C C23 1.14573(18) -0.03556(14) 0.67710(12) 0.0226(3) Uani d . 1 . .
    C C24 1.23947(19) -0.08211(15) 0.60366(13) 0.0271(4) Uani d . 1 . .
    H H24A 1.2029 -0.1121 0.5589 0.033 Uiso calc R 1 . .
    C C25 1.3875(2) -0.08246(16) 0.59918(13) 0.0308(4) Uani d . 1 . .
    H H25A 1.4519 -0.1129 0.5507 0.037 Uiso calc R 1 . .
    C C26 1.44221(19) -0.03750(16) 0.66696(13) 0.0297(4) Uani d . 1 . .
    H H26A 1.5428 -0.0391 0.6632 0.036 Uiso calc R 1 . .
    C C27 1.34872(18) 0.00941(15) 0.73970(12) 0.0249(4) Uani d . 1 . .
    H H27A 1.3855 0.0392 0.7846 0.030 Uiso calc R 1 . .
    C C28 1.19917(17) 0.01076(13) 0.74373(11) 0.0204(3) Uani d . 1 . .
    C C29 1.07917(17) 0.05268(13) 0.81917(11) 0.0193(3) Uani d . 1 . .
    C C30 1.4823(3) 0.4233(2) 0.25134(19) 0.0510(6) Uani d . 1 . .
    H H30A 1.5176 0.3737 0.2062 0.077 Uiso calc R 1 . .
    H H30B 1.5639 0.4021 0.3046 0.077 Uiso calc R 1 . .
    H H30C 1.4510 0.5119 0.2043 0.077 Uiso calc R 1 . .
    C C31 0.1659(2) 0.4899(2) 0.9091(2) 0.0500(5) Uani d . 1 . .
    H H31A 0.0674 0.4950 0.8860 0.075 Uiso calc R 1 . .
    H H31B 0.1772 0.5712 0.8725 0.075 Uiso calc R 1 . .
    H H31C 0.1737 0.4660 0.9886 0.075 Uiso calc R 1 . .
    C C32 0.96162(18) -0.19190(14) 0.92734(13) 0.0253(4) Uani d . 1 . .
    H H32A 0.9288 -0.2336 0.9988 0.038 Uiso calc R 1 . .
    H H32B 1.0701 -0.2098 0.9341 0.038 Uiso calc R 1 . .
    H H32C 0.9395 -0.2223 0.8743 0.038 Uiso calc R 1 . .
    H H1O2 1.115(3) 0.022(2) 0.972(2) 0.053(7) Uiso d . 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 C9 . 1.2183(18) ?
    O2 C29 . 1.4033(17) ?
    O2 H1O2 . 0.85(3) ?
    O3 C22 . 1.2211(18) ?
    N1 C12 . 1.4703(18) ?
    N1 C11 . 1.4738(19) ?
    N1 C29 . 1.4845(18) ?
    N2 C32 . 1.4637(19) ?
    N2 C20 . 1.469(2) ?
    N2 C21 . 1.4723(18) ?
    C1 C2 . 1.386(2) ?
    C1 C6 . 1.403(2) ?
    C1 H1A . 0.93 ?
    C2 C3 . 1.392(3) ?
    C2 H2A . 0.93 ?
    C3 C4 . 1.390(3) ?
    C3 C30 . 1.505(2) ?
    C4 C5 . 1.380(2) ?
    C4 H4A . 0.93 ?
    C5 C6 . 1.399(2) ?
    C5 H5A . 0.93 ?
    C6 C7 . 1.462(2) ?
    C7 C8 . 1.344(2) ?
    C7 H7A . 0.93 ?
    C8 C9 . 1.498(2) ?
    C8 C12 . 1.524(2) ?
    C9 C10 . 1.533(2) ?
    C10 C19 . 1.540(2) ?
    C10 C21 . 1.5530(19) ?
    C10 C11 . 1.5569(19) ?
    C11 H11A . 0.97 ?
    C11 H11B . 0.97 ?
    C12 H12A . 0.97 ?
    C12 H12B . 0.97 ?
    C13 C14 . 1.384(2) ?
    C13 C18 . 1.393(2) ?
    C13 H13A . 0.93 ?
    C14 C15 . 1.388(2) ?
    C14 H14A . 0.93 ?
    C15 C16 . 1.388(3) ?
    C15 C31 . 1.507(2) ?
    C16 C17 . 1.385(2) ?
    C16 H16A . 0.93 ?
    C17 C18 . 1.393(2) ?
    C17 H17A . 0.93 ?
    C18 C19 . 1.515(2) ?
    C19 C20 . 1.547(2) ?
    C19 H19A . 0.98 ?
    C20 H20A . 0.97 ?
    C20 H20B . 0.97 ?
    C21 C22 . 1.536(2) ?
    C21 C29 . 1.572(2) ?
    C22 C23 . 1.468(2) ?
    C23 C28 . 1.394(2) ?
    C23 C24 . 1.396(2) ?
    C24 C25 . 1.376(2) ?
    C24 H24A . 0.93 ?
    C25 C26 . 1.400(2) ?
    C25 H25A . 0.93 ?
    C26 C27 . 1.389(2) ?
    C26 H26A . 0.93 ?
    C27 C28 . 1.387(2) ?
    C27 H27A . 0.93 ?
    C28 C29 . 1.518(2) ?
    C30 H30A . 0.96 ?
    C30 H30B . 0.96 ?
    C30 H30C . 0.96 ?
    C31 H31A . 0.96 ?
    C31 H31B . 0.96 ?
    C31 H31C . 0.96 ?
    C32 H32A . 0.96 ?
    C32 H32B . 0.96 ?
    C32 H32C . 0.96 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C29 O2 H1O2 . . 112.9(16) ?
    C12 N1 C11 . . 108.58(11) ?
    C12 N1 C29 . . 114.54(11) ?
    C11 N1 C29 . . 104.38(11) ?
    C32 N2 C20 . . 112.70(12) ?
    C32 N2 C21 . . 116.01(12) ?
    C20 N2 C21 . . 107.99(11) ?
    C2 C1 C6 . . 120.88(15) ?
    C2 C1 H1A . . 119.6 ?
    C6 C1 H1A . . 119.6 ?
    C1 C2 C3 . . 121.48(16) ?
    C1 C2 H2A . . 119.3 ?
    C3 C2 H2A . . 119.3 ?
    C4 C3 C2 . . 117.59(16) ?
    C4 C3 C30 . . 121.49(17) ?
    C2 C3 C30 . . 120.92(18) ?
    C5 C4 C3 . . 121.40(16) ?
    C5 C4 H4A . . 119.3 ?
    C3 C4 H4A . . 119.3 ?
    C4 C5 C6 . . 121.44(16) ?
    C4 C5 H5A . . 119.3 ?
    C6 C5 H5A . . 119.3 ?
    C5 C6 C1 . . 117.17(14) ?
    C5 C6 C7 . . 117.71(14) ?
    C1 C6 C7 . . 125.12(14) ?
    C8 C7 C6 . . 130.04(14) ?
    C8 C7 H7A . . 115.0 ?
    C6 C7 H7A . . 115.0 ?
    C7 C8 C9 . . 116.81(13) ?
    C7 C8 C12 . . 124.92(14) ?
    C9 C8 C12 . . 118.11(12) ?
    O1 C9 C8 . . 121.97(13) ?
    O1 C9 C10 . . 121.88(14) ?
    C8 C9 C10 . . 116.16(12) ?
    C9 C10 C19 . . 113.59(12) ?
    C9 C10 C21 . . 112.47(12) ?
    C19 C10 C21 . . 105.14(11) ?
    C9 C10 C11 . . 105.65(11) ?
    C19 C10 C11 . . 119.93(12) ?
    C21 C10 C11 . . 99.28(11) ?
    N1 C11 C10 . . 103.44(11) ?
    N1 C11 H11A . . 111.1 ?
    C10 C11 H11A . . 111.1 ?
    N1 C11 H11B . . 111.1 ?
    C10 C11 H11B . . 111.1 ?
    H11A C11 H11B . . 109.0 ?
    N1 C12 C8 . . 114.17(12) ?
    N1 C12 H12A . . 108.7 ?
    C8 C12 H12A . . 108.7 ?
    N1 C12 H12B . . 108.7 ?
    C8 C12 H12B . . 108.7 ?
    H12A C12 H12B . . 107.6 ?
    C14 C13 C18 . . 120.67(15) ?
    C14 C13 H13A . . 119.7 ?
    C18 C13 H13A . . 119.7 ?
    C13 C14 C15 . . 121.66(16) ?
    C13 C14 H14A . . 119.2 ?
    C15 C14 H14A . . 119.2 ?
    C14 C15 C16 . . 117.66(15) ?
    C14 C15 C31 . . 121.37(17) ?
    C16 C15 C31 . . 120.96(17) ?
    C17 C16 C15 . . 121.05(15) ?
    C17 C16 H16A . . 119.5 ?
    C15 C16 H16A . . 119.5 ?
    C16 C17 C18 . . 121.23(16) ?
    C16 C17 H17A . . 119.4 ?
    C18 C17 H17A . . 119.4 ?
    C13 C18 C17 . . 117.73(15) ?
    C13 C18 C19 . . 122.55(14) ?
    C17 C18 C19 . . 119.72(14) ?
    C18 C19 C10 . . 114.91(12) ?
    C18 C19 C20 . . 115.93(13) ?
    C10 C19 C20 . . 104.77(11) ?
    C18 C19 H19A . . 106.9 ?
    C10 C19 H19A . . 106.9 ?
    C20 C19 H19A . . 106.9 ?
    N2 C20 C19 . . 106.63(12) ?
    N2 C20 H20A . . 110.4 ?
    C19 C20 H20A . . 110.4 ?
    N2 C20 H20B . . 110.4 ?
    C19 C20 H20B . . 110.4 ?
    H20A C20 H20B . . 108.6 ?
    N2 C21 C22 . . 114.83(11) ?
    N2 C21 C10 . . 102.80(11) ?
    C22 C21 C10 . . 114.00(11) ?
    N2 C21 C29 . . 114.35(11) ?
    C22 C21 C29 . . 105.28(11) ?
    C10 C21 C29 . . 105.45(11) ?
    O3 C22 C23 . . 127.68(14) ?
    O3 C22 C21 . . 123.96(14) ?
    C23 C22 C21 . . 108.36(12) ?
    C28 C23 C24 . . 121.26(15) ?
    C28 C23 C22 . . 110.20(13) ?
    C24 C23 C22 . . 128.53(14) ?
    C25 C24 C23 . . 118.28(15) ?
    C25 C24 H24A . . 120.9 ?
    C23 C24 H24A . . 120.9 ?
    C24 C25 C26 . . 120.64(15) ?
    C24 C25 H25A . . 119.7 ?
    C26 C25 H25A . . 119.7 ?
    C27 C26 C25 . . 121.11(15) ?
    C27 C26 H26A . . 119.4 ?
    C25 C26 H26A . . 119.4 ?
    C28 C27 C26 . . 118.36(14) ?
    C28 C27 H27A . . 120.8 ?
    C26 C27 H27A . . 120.8 ?
    C27 C28 C23 . . 120.35(14) ?
    C27 C28 C29 . . 127.57(13) ?
    C23 C28 C29 . . 112.01(13) ?
    O2 C29 N1 . . 110.03(11) ?
    O2 C29 C28 . . 107.24(11) ?
    N1 C29 C28 . . 116.66(12) ?
    O2 C29 C21 . . 113.48(11) ?
    N1 C29 C21 . . 105.34(11) ?
    C28 C29 C21 . . 104.15(11) ?
    C3 C30 H30A . . 109.5 ?
    C3 C30 H30B . . 109.5 ?
    H30A C30 H30B . . 109.5 ?
    C3 C30 H30C . . 109.5 ?
    H30A C30 H30C . . 109.5 ?
    H30B C30 H30C . . 109.5 ?
    C15 C31 H31A . . 109.5 ?
    C15 C31 H31B . . 109.5 ?
    H31A C31 H31B . . 109.5 ?
    C15 C31 H31C . . 109.5 ?
    H31A C31 H31C . . 109.5 ?
    H31B C31 H31C . . 109.5 ?
    N2 C32 H32A . . 109.5 ?
    N2 C32 H32B . . 109.5 ?
    H32A C32 H32B . . 109.5 ?
    N2 C32 H32C . . 109.5 ?
    H32A C32 H32C . . 109.5 ?
    H32B C32 H32C . . 109.5 ?
loop_
    _geom_torsion_atom_site_label_1
    _geom_torsion_atom_site_label_2
    _geom_torsion_atom_site_label_3
    _geom_torsion_atom_site_label_4
    _geom_torsion_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 0.4(2) ?
    C1 C2 C3 C4 . . . . 1.3(2) ?
    C1 C2 C3 C30 . . . . -178.91(16) ?
    C2 C3 C4 C5 . . . . -1.4(3) ?
    C30 C3 C4 C5 . . . . 178.74(17) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C4 C5 C6 C1 . . . . 1.7(2) ?
    C4 C5 C6 C7 . . . . -178.52(15) ?
    C2 C1 C6 C5 . . . . -1.9(2) ?
    C2 C1 C6 C7 . . . . 178.37(14) ?
    C5 C6 C7 C8 . . . . 156.33(16) ?
    C1 C6 C7 C8 . . . . -23.9(3) ?
    C6 C7 C8 C9 . . . . -176.56(14) ?
    C6 C7 C8 C12 . . . . -1.3(3) ?
    C7 C8 C9 O1 . . . . -24.1(2) ?
    C12 C8 C9 O1 . . . . 160.29(14) ?
    C7 C8 C9 C10 . . . . 156.00(13) ?
    C12 C8 C9 C10 . . . . -19.64(18) ?
    O1 C9 C10 C19 . . . . -2.6(2) ?
    C8 C9 C10 C19 . . . . 177.34(12) ?
    O1 C9 C10 C21 . . . . 116.68(15) ?
    C8 C9 C10 C21 . . . . -63.39(16) ?
    O1 C9 C10 C11 . . . . -136.04(14) ?
    C8 C9 C10 C11 . . . . 43.90(15) ?
    C12 N1 C11 C10 . . . . 76.80(13) ?
    C29 N1 C11 C10 . . . . -45.79(13) ?
    C9 C10 C11 N1 . . . . -71.79(13) ?
    C19 C10 C11 N1 . . . . 158.37(12) ?
    C21 C10 C11 N1 . . . . 44.82(13) ?
    C11 N1 C12 C8 . . . . -50.37(15) ?
    C29 N1 C12 C8 . . . . 65.83(16) ?
    C7 C8 C12 N1 . . . . -154.02(14) ?
    C9 C8 C12 N1 . . . . 21.23(18) ?
    C18 C13 C14 C15 . . . . 0.7(3) ?
    C13 C14 C15 C16 . . . . 0.3(3) ?
    C13 C14 C15 C31 . . . . -178.27(17) ?
    C14 C15 C16 C17 . . . . -0.8(2) ?
    C31 C15 C16 C17 . . . . 177.68(17) ?
    C15 C16 C17 C18 . . . . 0.5(3) ?
    C14 C13 C18 C17 . . . . -1.0(2) ?
    C14 C13 C18 C19 . . . . 178.92(15) ?
    C16 C17 C18 C13 . . . . 0.5(2) ?
    C16 C17 C18 C19 . . . . -179.51(14) ?
    C13 C18 C19 C10 . . . . -81.59(18) ?
    C17 C18 C19 C10 . . . . 98.37(16) ?
    C13 C18 C19 C20 . . . . 41.0(2) ?
    C17 C18 C19 C20 . . . . -139.06(15) ?
    C9 C10 C19 C18 . . . . -91.75(15) ?
    C21 C10 C19 C18 . . . . 144.87(12) ?
    C11 C10 C19 C18 . . . . 34.47(18) ?
    C9 C10 C19 C20 . . . . 139.85(12) ?
    C21 C10 C19 C20 . . . . 16.48(14) ?
    C11 C10 C19 C20 . . . . -93.92(15) ?
    C32 N2 C20 C19 . . . . -155.70(12) ?
    C21 N2 C20 C19 . . . . -26.24(15) ?
    C18 C19 C20 N2 . . . . -122.78(13) ?
    C10 C19 C20 N2 . . . . 4.99(15) ?
    C32 N2 C21 C22 . . . . 39.35(17) ?
    C20 N2 C21 C22 . . . . -88.23(14) ?
    C32 N2 C21 C10 . . . . 163.73(12) ?
    C20 N2 C21 C10 . . . . 36.15(14) ?
    C32 N2 C21 C29 . . . . -82.52(15) ?
    C20 N2 C21 C29 . . . . 149.89(12) ?
    C9 C10 C21 N2 . . . . -155.97(11) ?
    C19 C10 C21 N2 . . . . -31.88(13) ?
    C11 C10 C21 N2 . . . . 92.73(12) ?
    C9 C10 C21 C22 . . . . -31.04(17) ?
    C19 C10 C21 C22 . . . . 93.04(14) ?
    C11 C10 C21 C22 . . . . -142.35(12) ?
    C9 C10 C21 C29 . . . . 83.93(13) ?
    C19 C10 C21 C29 . . . . -151.98(11) ?
    C11 C10 C21 C29 . . . . -27.37(13) ?
    N2 C21 C22 O3 . . . . 53.63(19) ?
    C10 C21 C22 O3 . . . . -64.61(19) ?
    C29 C21 C22 O3 . . . . -179.69(13) ?
    N2 C21 C22 C23 . . . . -125.69(13) ?
    C10 C21 C22 C23 . . . . 116.07(13) ?
    C29 C21 C22 C23 . . . . 0.98(14) ?
    O3 C22 C23 C28 . . . . 179.97(14) ?
    C21 C22 C23 C28 . . . . -0.75(16) ?
    O3 C22 C23 C24 . . . . -1.6(3) ?
    C21 C22 C23 C24 . . . . 177.64(14) ?
    C28 C23 C24 C25 . . . . 0.6(2) ?
    C22 C23 C24 C25 . . . . -177.60(15) ?
    C23 C24 C25 C26 . . . . 0.2(2) ?
    C24 C25 C26 C27 . . . . -0.5(3) ?
    C25 C26 C27 C28 . . . . 0.0(2) ?
    C26 C27 C28 C23 . . . . 0.8(2) ?
    C26 C27 C28 C29 . . . . 177.55(14) ?
    C24 C23 C28 C27 . . . . -1.1(2) ?
    C22 C23 C28 C27 . . . . 177.39(13) ?
    C24 C23 C28 C29 . . . . -178.35(13) ?
    C22 C23 C28 C29 . . . . 0.17(17) ?
    C12 N1 C29 O2 . . . . 145.71(12) ?
    C11 N1 C29 O2 . . . . -95.69(12) ?
    C12 N1 C29 C28 . . . . 23.31(17) ?
    C11 N1 C29 C28 . . . . 141.90(12) ?
    C12 N1 C29 C21 . . . . -91.62(13) ?
    C11 N1 C29 C21 . . . . 26.98(13) ?
    C27 C28 C29 O2 . . . . -55.96(19) ?
    C23 C28 C29 O2 . . . . 121.01(13) ?
    C27 C28 C29 N1 . . . . 67.89(19) ?
    C23 C28 C29 N1 . . . . -115.14(14) ?
    C27 C28 C29 C21 . . . . -176.52(14) ?
    C23 C28 C29 C21 . . . . 0.45(15) ?
    N2 C21 C29 O2 . . . . 9.84(17) ?
    C22 C21 C29 O2 . . . . -117.13(12) ?
    C10 C21 C29 O2 . . . . 122.01(12) ?
    N2 C21 C29 N1 . . . . -110.58(12) ?
    C22 C21 C29 N1 . . . . 122.45(11) ?
    C10 C21 C29 N1 . . . . 1.59(14) ?
    N2 C21 C29 C28 . . . . 126.12(12) ?
    C22 C21 C29 C28 . . . . -0.85(14) ?
    C10 C21 C29 C28 . . . . -121.71(12) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    O2 H1O2 N2 2_757 0.85(2) 2.00(2) 2.794(2) 156(2) yes
    C5 H5A O3 2_756 0.93 2.48 3.206(2) 135 yes
    C11 H11B O2 2_757 0.97 2.36 3.258(2) 154 yes
    C13 H13A O2 2_757 0.93 2.40 3.291(2) 161 yes
    C30 H30C Cg1 2_766 0.96 2.83 3.563(3) 134 yes
